One-Pot Synthesis of Bis(arylamino)pentiptycenes by TiCl 4 -DABCO Assisted Reductive Amination of Pentiptycene Quinone.
- Resource Type
- Academic Journal
- Authors
- Zhang ZJ; Department of Chemistry, National Taiwan University, Taipei, 10617, Taiwan.; Hsu YF; Department of Chemistry, National Taiwan University, Taipei, 10617, Taiwan.; Kao CC; Department of Chemistry, National Taiwan University, Taipei, 10617, Taiwan.; Yang JS; Department of Chemistry, National Taiwan University, Taipei, 10617, Taiwan.
- Source
- Publisher: American Chemical Society Country of Publication: United States NLM ID: 100890393 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1523-7052 (Electronic) Linking ISSN: 15237052 NLM ISO Abbreviation: Org Lett Subsets: PubMed not MEDLINE; MEDLINE
- Subject
- Language
- English
The previously eight-step synthesis of bis(arylamino)pentiptycenes ( 2 ) from pentiptycene quinone ( 1 ) can now be achieved in a single step with 18-90% yields through TiCl 4 -DABCO assisted reductive amination with anilines. Both the dual amination of 1 and the in situ reduction of quinone diimines are unprecedented. The π system of 2 can be further expanded, including the formation of bis(diarylamino)pentiptycenes. This work also provides mechanistic insights into the challenges encountered in the dual reductive amination of 1 with other amines.